The sexy tomboy prefers her man's oversize button-down to a strappy garter getup any day and feels right at home in a tiny pair of briefs. Think Calvin Klein underwear ads, Sigourney Weaver in Alien, and Freja Beha Erichsen's perfect bedhead. She may be low-key, but she's still high-fashion — and proves that you can totally be seductive while staying on the sporty side. Click through to see all of my picks for the hot-to-trot tomboy.